Acetic Acid → 4-(Cyclopropylamino)-1-(trifluoromethyl)cyclohexanol

HRID 509286Notes

Reaction equation

HRID 509286 reaction equation
[OH:1][C:2]1([C:9]([F:12])([F:11])[F:10])[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[CH:13]1([NH2:16])[CH2:15][CH2:14]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C.[OH-].[Na+]>ClCCCl>[CH:13]1([NH:16][CH:5]2[CH2:6][CH2:7][C:2]([C:9]([F:12])([F:11])[F:10])([OH:1])[CH2:3][CH2:4]2)[CH2:15][CH2:14]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 69828CyclopropylamineHCID 5049666Sodium triacetoxyborohydrideHCID 200351424-Hydroxy-4-(trifluoromethyl)cyclohexan-1-one

Product 1

HCID 674665704-(Cyclopropylamino)-1-(trifluoromethyl)cyclohexanolYield 93%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

4-hydroxy-4-(trifluoromethyl)cyclohexanone (570 mg, 3.13 mmol) was dissolved in 1,2-dichloroethane (20 ml), followed by sequential addition of cyclopropylamine (0.24 ml, 3.44 mmol), NaBH(OAc)3 (1.06 g, 5.01 mmol), and acetic acid (0.18 ml, 3.13 mmol), and then the resulting mixture was stirred at room temperature under nitrogen stream for 13 hours. The resulting reaction liquid was neutralized by addition of 10% aqueous NaOH solution, and extracted with 5% MeOH/MC (20 ml×3). The organic layer was dried over anhydrous sodium sulfate, followed by filtration, concentration, and vacuum drying, to obtain 650 mg of yellow solid (93%).

Workup

  1. customThe resulting reaction liquid
  2. extractionextracted with 5% MeOH/MC (20 ml×3)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfollowed by filtration, concentration, and vacuum
  5. customdrying

Sources & evidence

ORD record
ord-51202efc476144d9aeab2716857befd5
Source dataset
uspto-grants-2015_08
Patent number
US09096571B2

Reaction notes

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